C–H activation

Rogge, Torben; Kaplaneris, Nikolaos; Chatani, Naoto; Kim, Jinwoo; Chang, Sukbok; Punji, Benudhar; Schafer, Laurel L.; Musaev, Djamaladdin G.; Wencel‐Delord, Joanna; Roberts, Charis A.; Sarpong, Richmond; Wilson, Zoe E.; Brimble, Margaret A.; Johansson, Magnus J.; Ackermann, Lutz

doi:10.1038/s43586-021-00041-2

Cited by 371 publications

(230 citation statements)

References 409 publications

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“…Another promising pathway to promote the regioselectivity of DArP that emerged recently is the judicious utilization of directing groups in the monomer design. Although a variety of directing groups have been widely incorporated in small-molecule C H activation to improve the reactivity and selectivity, [175][176][177][178]224,225 the employment of such a strategy in DArP remains limited. Moreover, broadening and refining efficient catalytic systems for DArP to be compatible and tolerable with different functional groups and structural motifs will continue to be an attractive subject of interest, 226 since such functionalized monomers are generally incompatible with Stille or Suzuki.…”

Section: Discussionmentioning

confidence: 99%

Improving the efficiency and sustainability of catalysts for direct arylation polymerization (DArP)

Thompson

2021

Journal of Polymer Science

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In the past decade, direct arylation polymerization (DArP) has rapidly developed as a sustainable synthetic protocol for cost-effective, atom-economical preparation of conjugated polymers. By circumventing monomer functionalization with toxic transmetallating reagents such as organostannane and organoboron required for Stille-Migita and Suzuki-Miyaura polymerization methods, DArP proceeds through a metal-catalyzed C H activation pathway for the preparation of highperformance conjugated polymer materials. This review evaluates the development of several classes of efficient catalysts/catalytic systems from small-molecule studies to polymerizations, including the mechanisms involved in these transformations and how they inspire catalyst and monomer design for defect-free conjugated polymer synthesis. Recent advances in developing more sustainable first-row transition metal catalysts for DArP are also highlighted, and the fundamental understanding of these efficient and sustainable catalysts should motivate the pursuit for the next generation of catalytic design to enable more effective and environmentally friendly conjugated polymer synthesis.

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Section: Discussionmentioning

confidence: 99%

Improving the efficiency and sustainability of catalysts for direct arylation polymerization (DArP)

Thompson

2021

Journal of Polymer Science

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“…The impact of single atom changes in small molecules on the intermolecular interactions with their biological targets is well-documented. 1 With the development of site-selective functionalization reactions, 2 the isosteric replacement of an atom on the periphery of a complex molecule has become increasingly practical. In contrast, the analogous process for an atom embedded in the molecular skeleton remains challenging.…”

Section: Introductionmentioning

confidence: 99%

A C-to-O atom-swapping reaction sequence enabled by Ni-catalyzed decarbonylation of lactones

Luu

2022

Chem. Sci.

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“…Of particular interest are late-stage functionalizations (LSF), 8 , 9 where the controlled chemoselective transformation of the desired C–H bonds in complex drug-like molecules has the potential to greatly aid in the hit-to-lead and lead optimization processes. 10 Bypassing the need for time-, material-, and labor-intensive de novo synthesis of analogues would greatly aid in structure–activity relationship (SAR) studies or even the generation of new candidate drugs. In terms of desirable transformations, the introduction of small functional groups such as −CH 3 , −CF 3 , −NH 2 , −OH, and −F is of highest priority and would be widely used in the industry.…”

Section: Introductionmentioning

confidence: 99%

Merging Directed C–H Activations with High-Throughput Experimentation: Development of Iridium-Catalyzed C–H Aminations Applicable to Late-Stage Functionalization

Weis

Johansson

Korsgren

et al. 2022

JACS Au

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Herein, we report an iridium-catalyzed directed C–H amination methodology developed using a high-throughput experimentation (HTE)-based strategy, applicable for the needs of automated modern drug discovery. The informer library approach for investigating the accessible directing group chemical space, in combination with functional group tolerance screening and substrate scope investigations, allowed for the generation of reaction application guidelines to aid future users. Applicability to late-stage functionalization of complex drugs and natural products, in combination with multiple deprotection protocols leading to the desirable aniline matched pairs, serve to demonstrate the utility of the method for drug discovery. Finally, reaction miniaturization to a nanomolar range highlights the opportunities for more sustainable screening with decreased material consumption.

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C–H activation

Cited by 371 publications

References 409 publications

Improving the efficiency and sustainability of catalysts for direct arylation polymerization (DArP)

Improving the efficiency and sustainability of catalysts for direct arylation polymerization (DArP)

A C-to-O atom-swapping reaction sequence enabled by Ni-catalyzed decarbonylation of lactones

Merging Directed C–H Activations with High-Throughput Experimentation: Development of Iridium-Catalyzed C–H Aminations Applicable to Late-Stage Functionalization

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